How ADHD Traits Impact Small Business Owner with Diann Wingert

How ADHD Traits Can Impact a Small Business Owner with Diann Wingert

Hey everyone. Welcome to The Bold Money Revolution Podcast. I’m here gracing your presence with my dear friend and my sister from another mister, Diann Wingert. She is a therapist by training and a coach by choice and we are both ADHDers. At one point, when I first stumbled upon Diann online, she was coaching people with ADHD, but that has seem to have now left her area of expertise, so I want to have a conversation with Diann today about the intersection of ADHD-like traits, of distractibility, impulsivity, and entrepreneurship. Welcome, Diann.

Diann Wingert: this is one of my favorite conversations so thank you for inviting me to have it, especially with you.

Tara Newman: Yeah, absolutely. Where are we going to start with this? Kick us off. What’s the top thing that we need to be talking about here in terms of entrepreneurship and the way we work, really, that’s what this is going to come down to, how we as humans work.

Diann Wingert: Yes, well first of all, I want to start us off with some basic facts about being a woman with ADHD. Because if you are a woman and you suspect you have ADHD, you probably do, and the reason why I say that is because most females are not diagnosed in childhood, most males are. The bottom line for that is that most females do not have as much physical hyperactivity as boys do and it is the physical hyperactivity that little boys with ADHD have that cause them to be disruptive in the classroom, and teachers do not want to deal with that so they get identified, they get referred, they oftentimes get medicated.

Girls, partly because we have more connections between our right and left hemispheres, partly because we’re easier to socialize and condition to other people’s expectations, and partly because the majority of us are not as physically hyperactive, most girls will not disrupt the classroom. Now I have combined type ADHD, I suspect you do too, and combined type ADHD means our physical hyperactivity manifests in the following ways: we talk a lot, we are very curious, we are always in need of something to do, we’re constantly starting new projects, may not necessarily finish them, and none of that is necessarily a problem for a school teacher.

Girls who become women usually don’t find out that they have ADHD until much later in the game. By the time they do, they are usually dealing with one or more of the following: an eating disorder, an addictive or alcohol problem, a spending problem, and usually there’s anxiety and/or depression on board, because when you can’t make your life work, you can’t make your relationships work, you literally don’t feel like you can get yourself together. You’re going to eventually have a lot of anxiety because you’re going to be very self-conscious about how other people perceive you, how you perceive yourself, and eventually, you just wear yourself out and become depressed.

But I’m a little bit concerned about the fact that there are literally tons of people right now who are identifying themselves as ADHD and talking about themselves as having ADHD. If you’re on TikTok, you can’t escape the awareness of this, like everybody on TikTok is an ADHD expert suddenly, but not everybody who has ADHD traits would actually qualify for the diagnosis. This is a critical factor because most entrepreneurs have these traits with or without a diagnosis.

Tara Newman: Can we talk about TikTok for a second?

Diann Wingert: Love to.

Tara Newman: TikTok hurts my brain and I tell myself that’s because of my ADHD. It makes it very, very bad. Are you able to like the eight seconds and the constant scrolling? It agitates the hell out of my brain so I’m like, “Well, if you’re on TikTok getting ADHD advice and you think you have ADHD, maybe it’s just TikTok unless you actually have ADHD.”

Diann Wingert: Okay, listen. We both know that all social media platforms are deliberately engineered to hook us, reel us in, and hold us captive. That’s what they’re there for and they’re very very good at it. TikTok is the new kid on the block. One of the reasons why it’s growing faster than any social media platform has a right to do and faster than any of the others have is because of the short-form content that is very stimulating to all brains, but especially to ADHD brains, maybe over stimulating to yours. But I think the other thing is that hooks and captivates a lot of people, especially those with ADHD because you don’t really know what’s going to show up in your feed. That’s the magic of TikTok.

Every other social media platform, yes, you’re going to see some stuff you don’t expect to see but you’re mostly going to see stuff that you asked to see by following or liking somebody’s stuff. With TikTok, they suggest things to you based on what you have viewed in the past. The element of surprise is like crack for most people with ADHD because we always love novelty. Now for you, I think you’ve trained your brain, you wouldn’t be good with money, you’ve trained your brain and maybe it’s just so rapid, so much change that it’s disruptive and doesn’t make you happy, but literally, I could stay there for eight hours. I have to set a timer to make sure it sounds.

This is another thing I should say, Tara, everybody who has ADHD or is ADHD, because you can say I am ADHD or I have ADHD, they’re both fine, it’s just an identification issue, we’re not all the same, like first of all, there are three different types. There’s predominantly inattentive distractible, predominantly hyperactive-impulsive, and combined, which is me, and I suspect you, but even within those categories, there are tons and tons and tons of other things. People can have dyslexia, they can have other learning disabilities, they can have OCD, they can have so many others. There are a lot of things that travel with ADHD. But not everybody’s ADHD looks the same. I love TikTok, you are like, “No. Hard no.” So no wonder there are so many so-called experts because it’s confusing.

Tara Newman: It is confusing. Thank you. Thank you for sharing that. Let’s talk about how this helps or inhibits entrepreneurship.

Diann Wingert: Yes. This is actually a really, really great question. One of the things I think is confusing about ADHD is that there’s a big camp that’s like “This is a disorder. This is a downright disability.” If you have ADHD, let me just say that you’re more likely to have an addiction, you’re more likely to have a bunch of unpaid traffic tickets, you’re more likely to be divorced, you’re more likely to lose your job, you’re more likely to go to jail, all of those things are true. How is it possible that this disabling disorder that, statistically speaking, could cause you to drop out of school, become an addict, become homeless, go to jail, can’t keep a job, can’t keep a relationship, and we have plenty of data out there, how is it possible that other people call this very same condition the entrepreneurial superpower? How’s that possible?

Here’s what I think. I think when it comes to ADHD, and while I don’t like to call myself an expert of anything, I call myself a lifelong learner and a relentlessly curious human, so if I’m interested in something, I just do a face plant into everything that’s ever been said about it and just keep going. I have ADHD. I’ve lovingly passed it on to all three of my kids, thanks, Mom, before I knew I had it, and I’ve been working in the field first as a psychotherapist for many years and then many, many of my clients have ADHD.

I think the number one thing that will either help ADHD be in a way an unfair advantage, Tara, or a hindrance, is goodness of fit between you and your environment, meaning if you are a person who doesn’t want to sit still, don’t. For the love of God, get a desk job. But you could be a park ranger. People like us need to have environments for work and the rest of life that are well suited to our minds and brains. If you’re able to pull that off, the two most important things I agree with Dr. Ned Hallowell on these two things, the two most important things a person with ADHD needs to do are choose the right career path and choose the right partner.

Why do so many of us choose entrepreneurship? I think the reason why so many of us choose entrepreneurship is because we literally get to write our own ticket. Think about it when you take a job, you are given a job description, and in most environments, you will be told how to do it. I think of ADHD as more like when I was in school and I got a math problem, I only got credit for getting the right answer if I could show my work, but people with ADHD are neurodivergent. We go about things differently. We need to do things our way. So if my way of getting to the right answer wasn’t the approved way, I didn’t get credit, but it’s like, “But wait a minute, I got the right answer?” Yes, but you didn’t go about it the right way.

Well, when you’re an entrepreneur, you get to decide what the right way is for you, you do not necessarily have to follow the prescribed course of action, so that is extremely appealing. Also people with ADHD tend to be much more risk-tolerant. I think this comes from the fact that most of us are much more impulsive. We literally take a flying leap into something before we’ve really thought it through. I like to say we go off the high dive without checking if there’s water in the pool, and then on the way down, we automagically figure out a parachute or something rather, but you have to be a risk taker to start a business.

If you’re also a quick problem solver, a creative problem solver, an out-of-the-box thinker, then even though you may make a lot of mistakes because of those risks, you often figure out what you need to do to fix them. The third trait is we tend to get over things much more quickly than other people. It’s because we always want to move on, so we make a mistake, we’re like, “Oh, I wish I hadn’t done that, well, that really sucks. That wasn’t what I had in mind. Well, you know what, it’s not so bad. I’m going to do this instead,” and then we just move on.

Whereas sometimes, if you have a marital partner or your team, they’re like, “What just happened?” If they don’t have ADHD, they need to process what happened, we’re already on to the next thing. You can see how this personality type is quick ideas, quick to act, more resilient because people who are risk-takers tend to make more mistakes in general, so if we can then figure out how to course correct from that and move on, I don’t think it’s a superpower necessarily, but if you have ADHD and you know how to leverage the strengths and manage the struggles, I think it definitely can be an advantage.

Tara Newman: Yeah, because for me, I can say that I think my self-awareness plus the ADHD is what became my superpower. I was aware that I was struggling with things and I became curious about finding solutions for those struggles, which led me down a path of wild executive functioning skills through creating habits and structure. I’m an incredibly structured, process-driven checklist which sounds weird for an ADHD–

Diann Wingert: No, no, no, all the successful people with ADHD are like that.

Tara Newman: Thank you, thank you, because I didn’t get diagnosed until I was 44, and that’s when I started to experiment, as I call it, with medication, so I was like, “I can’t. This doesn’t feel good for me. How do I feel good?” I feel good with habits, structure, and process, and that all calms my nervous system, my anxiety, I don’t know if it necessarily calms my impulsivity because yes, I can be a quick decision-maker, I’m very okay with risk, I don’t give a lot of shits about a lot of things, so that stuff really resonates.

Two things that I think have particularly been challenging for me as a business owner that I’ve had to work through: one, rejection sensitivity. It’s really hard to do sales and have difficult conversations, which I know you and I both have a great skill set in; boundaries, those are all things that with my rejection sensitivity I think were really a struggle. The only reason why I was remotely decent at it is because they were actually challenging for me. I’ve really had to learn, and again, I think that curiosity.

Then the other thing is my brain can be really stubborn. Yes, impulsive, but I didn’t realize how stubborn my brain could be and how hard it could be for me to follow instruction or just do it the way other people are doing it. There’s no reason to recreate the wheel all the time. Yes, I can make it mine but follow the path of someone before you and let that inform how you can make it your own, not constantly trying to recreate the wheel, and when I stopped trying to constantly recreate the wheel and take what somebody else did and create a framework for it that allowed me to space to be creative and make it my own, that’s when my business really started to thrive, not stubbornly resisting everything because it was somebody else’s idea.

Diann Wingert: This is a really great example, Tara, of how a neurological difference the way our brains work becomes a personality trait. But with self-awareness and a willingness to figure it out, we can achieve mastery. What you just said was basically sometimes, my brain is really stubborn, and that is we can be very rigid about doing things our way. Because think about it this way, I don’t know what the current numbers are, because women over 40 are a very rapidly growing, group of people being identified and diagnosed with ADHD, but let’s say it’s something like 4.3%, don’t quote me, somewhere in the 4% category of adults have been diagnosed with ADHD.

I believe anecdotally that we make up about 10% of all adults, which means, so most people for every person that’s been officially diagnosed, there’s like two and a half people that haven’t, my math sucks by the way, but that means that either people are suspecting they may be diagnosable and refusing to be diagnosed because, let’s face it, who wants a disorder? This diagnosis needs a makeover because it has deficit and disorder in the name, it’s like thank you, but no, it needs a new title. It’s got a real PR problem, but people don’t want a stigmatizing diagnosis even though it’s probably less stigmatizing than it used to be so they don’t get diagnosed.

But also if you figure out how to work with these things and your life is not really impaired, you’re not actually diagnosable. This is the one thing that most people don’t understand. I also want to say something about rejection sensitivity. If you have all the traits, and you can go down the list, there are like 18 different things, if you have 11 of them, you meet the criteria, but just having those traits doesn’t mean you have ADHD. You have to have enough of the traits plus impairment.

Now many men who are successful entrepreneurs have a wife, girlfriend, secretary, executive assistant who are literally taking all of the executive functioning challenges off their plate and handling it for them so that man gets to just do what he does best and can be wildly successful. Meanwhile, I’ve worked with some of these wives and girlfriends, they are losing their shit on a regular basis because he can be difficult to manage, but is it actually a diagnosis if you don’t have the impairment? I say if you take away the supports, the people, and the structures that keep you focused, that allow you to follow through, and allow you to finish, if you take away those supports, are you impaired?

And yes, that’s how you could be diagnosed, that’s how I could be diagnosed, but most of the really, really successful people who have these traits, whether they’ve gotten themselves diagnosed or not, if they have a lot of structure in their life, they won’t be impaired, and structure like all behavior is habit forming if you don’t resist it or resent it. Now the rejection sensitivity, I’ve probably done 15 or 20 podcast interviews on this topic because something that makes me a little crazy is how many people who either just found out they have ADHD or they haven’t officially been diagnosed but suspect they do so they’ve claimed it, are talking about rejection sensitive dysphoria and they are calling it RSD. They’re treating it like it’s an additional diagnosis like OCD.

First of all, it’s a part of ADHD, it is not a separate diagnosis. It is also part of the makeup of most highly-creative people, most gifted people, almost all artists, empaths, highly sensitive, like ADHD folks don’t corner the market on rejection sensitivity. I just refer to it as rejection sensitivity, if you’re creative, if you’re gifted, if you have ADHD, if you’re an empath, if you’re highly sensitive, you will probably struggle with rejection, and that means you will probably be less likely to put yourself out there, probably less likely to really demonstrate your genuine gifts, less likely to ask for what you want, whether it’s money or other things in relationships.

If you perceive that you’re going to get a no or that they are thinking something negatively of you for asking, you will probably silence yourself to avoid the profound dysphoria, negative mood, low mood, a depressive mood that comes with that feeling of rejection. You don’t even have to be rejected, you have to perceive that you’re being rejected or that you are being thought of in a negative way. That covers a lot of territory, just like, “Well, I can’t put myself out there because people might not like it. That’ll shut you down.”

Tara Newman: Oh, gosh. This has probably been the single most painful part of being an entrepreneur, especially in the online business space for me. The torment and the torture of working through this over the last eight years have been, I don’t even know if I have words for it, it’s been painful, it’s been seriously painful, and people look at me and they’re like, “You’re so confident and you’re amazing,” and I’m like, “I don’t know how to explain to you how devastatingly hard this has been and how much I understand when you all come to me and you’re like, ‘I can’t do Facebook lives, I can’t do this, I can’t do that,’ I get it. Let’s find the things you can do.’”

Diann Wingert: And yet I’m certain, Tara, that you have found ways and continue to look for ways to manage it effectively. This is a lot of the work I do because if you are an entrepreneur, whether you might call yourself a freelancer or whatever, if you generate your own income from your own effort, you basically have to be in marketing and sales, you have to. Being in marketing and sales, which just very fundamentally means letting people know what you do, communicating the value of what you do, and inviting people to buy from you, you have to do that, and in order to do that effectively, you have to manage your rejection sensitivity because otherwise, it’ll stop you from ever sharing what you have to offer with other people because you will be so terrified that they may find fault with you.

It doesn’t even have to be about the value of what you do, it could be worrying as a woman that other people will think you’re too bold, like you use the word bold in your marketing, I use the word driven. I actually had a person tell me once that she decided not to work with me because I was too confident.

Tara Newman: “Yes, I’m too grounded or masculine.”

Diann Wingert: Oh, girl, we could really go on a wild ride about that. Actually now, because I happen to be very tall, and my name is Diann, I’m now referring to it as Big D energy because I want to own this masculine energy that I have been told all my life that I have, it used to confuse me. I think people used to use it to try to shut me down, and not just men, gay men love me by the way, straight men, not so much and other women not so much, but what I’ve learned is if I’m going to let them dominate me because I’m afraid of what they might think, I decide they’re probably thinking it anyway no matter what I do, no matter how much I try to dim it, suppress it, quiet it down, shut it down, and I need to be concerned about the people who will be attracted to it, not the ones who will throw shade on it.

I haven’t completed this and I work very hard on managing my mind because you can get completely hijacked by fear of what other people might think, ask yourself, just tell yourself they probably are, and? We try so hard to change our behavior because of what we think other people will think of our genuine behavior when in fact, no matter what you do, they’re probably going to think it anyway. If that’s so, so what? Well, they won’t like me. They weren’t going to like you anyway. But they might talk shit about me, possible, they may talk shit about me online to other people who wouldn’t like you. I think it’s a shortcut to finding your people to be all of who you are even though it means you are risking rejection on a bigger scale. I know you believe that too, even though it’s painful.

Tara Newman: Yeah, so that’s where I’ve basically landed. After all the years of turning myself inside out about, it’s not for me, my ADHD journey is the first thing that I realized when I was diagnosed was every single person’s objection to me, criticism of me, feedback of me on a performance appraisal, on a school form, my mother, was in relationship to an ADHD behavior, and so I grew up and have all these stories around filtering.

Because my impulsive speech was embarrassing or my impulsive speech wasn’t correct in some way. It took me a lot of therapy and coaching to move through that belief that I constantly have to filter. Then once I took the filter off and started to trust that I’m a good person, but trust that I’m a good person in that I’m not going to get myself into a situation that I can’t get myself out of, and if I did, I’ve got good communication skills, and I’m happy to apologize and make repair for what I might have said or done, I became less exhausted.

Diann Wingert: This is such a good reminder.

Tara Newman: Yeah. I started to free up so much time and space for the things that I could do that actually moved my business forward.

Diann Wingert: But I don’t think many people realize how much of their chronic fatigue, and I don’t mean the diagnosis of chronic fatigue syndrome, but like if you’re always tired, and many of us are, I don’t know how many people recognize that a significant percentage of that is from masking, a significant percentage of that is because we are literally layering who we actually are with all of these, it’s like putting on Instagram filters, we got one for freckles, you got one for red hair, you got one that makes you look like a dog, a horse, or whatever, but it’s like we have been doing that all of our lives.

Especially as women, if you were the inattentive, distractible type, you would be a dreamer, you would be sitting in the classroom looking out the window, watching the butterflies dance in the tree, you might be doodling on a piece of paper, or you might be in your head writing stories and fantasizing and you wouldn’t be a problem to anyone because you wouldn’t be disrupting anything, but you wouldn’t get very good grades. You will probably be thought of as not very smart and people would just lower their expectations for you and you would eventually adopt that.

If you are more the combined type, like I think you and I are, we probably were doing a little bit of wiggling, we might have been impatient to get out to recess, or maybe late getting back from lunch, we are probably too chatty for some people’s taste and that can get you a little bit of negative feedback, but I’ll tell you, a couple of the nicknames that I used to get were oblivious, I was called oblivious on a regular basis because if something wasn’t sufficiently interesting to me, I would just go into my head and I got so much fantasy material in there. I can always entertain myself.

But if I’m not interested in what’s going on around me, I would just go in my head and entertain myself with something else and then somebody would say something and expect a response from me or they would flat out ask, say my name and I’d be like, “Huh?” and you’re like, “You are just totally oblivious.” Well, I check out when I’m bored and so how you become exhausted is “Okay. I don’t check out, don’t check out, don’t check out, act like you’re interested, act like you’re paying attention, nod your head, smile,” all that stuff because people get offended when you aren’t paying attention but you’re not actually paying attention, you’re just pretending to be, and that is fucking exhausting.

It also becomes not even second nature, it becomes like your first nature because women are socially conditioned to be likable and so it is freaking exhausting. Once you take all that off, once you stop masking and you actually let people know who you are, some of them are not going to like it for real, and then maybe people you’ve known forever.

Tara Newman: Yeah. I tend to be the inattentive, although my thoughts are impulsive, when I do speak, it can be impulsive speech. It used to be terrifying for me as a kid in school because I would lose track of time. The bell would ring, the bell would ring and I would lose in huge chunks of time. I barely made it into college so I love everybody who thinks they have to be perfect, smart, and all these things to run a business, be successful and make money. But I barely made it into college. My grades were so poor even though I was really intelligent and bright.

I found very recently an insight that I had, and I’ve never shared this before anywhere, so good job, Diann, in holding a space, but what I realized was I started to become really dissatisfied with coaching and really struggle with it. I’ve coached my entire life. My background in industrial organizational psychology was the birthplace of coaching and people would ask me, they’d be like, “Why do you call yourself a coach when all these online shitty coaches exist?” and I’m like, “Well, that’s what I’ve just done. The online-business space didn’t create coaching. That’s just been who I am.”

It started to get really heavy and I started to get really burned out on it. I couldn’t figure out why until probably about six months ago when I realized that coaching competencies are the exact opposite of all the criticism that I have garnered in my life and that coaching for me is actually the mask, and really what I want to be doing is teaching.

That was so wildly shocking because coaching competencies are active listening, you reflect back, and you ask good questions and I’m someone who’s just telling people all the time, I’m like in advisory mode, I’m tell-assertive, I do stop and ask questions but it takes some thoughtful planning. It could be very draining if I’m doing it for hours a day like I had been coaching. So really my gift and where I’m happiest is teaching with really good coaching skills, but that the coach part of this was definitely a mask for me.

Diann Wingert: That makes so much sense, Tara, and what it also reminds me of is one of the questions I’m most frequently asked is “You’re a UCLA-educated, trained psychotherapist,” I have a master’s degree, I have a clinical license, I’m a board-certified diplomat, I’ve done tons and tons and tons of advanced training, “and you ‘gave all that up’ to become a coach?” which basically, anybody can be like, “You don’t have to be certified, you don’t have to be, it’s totally unregulated. You can literally call yourself a coach and boom, you’re a coach. Why would you do that?”

Even my husband was like, “Why are you leaving a profession of a highly-trained skilled professional to literally jump in the boat with all these randos?” and I don’t like the term coach either, for the record, I am one part strategist, one part consultant, one part mentor. I do some coaching but one of the main reasons why I left being a therapist, I had a very successful private practice for many years of being a professor of social work, created programs, lead programs, I was clinical director of a large agency, I was definitely on the academic path the last five years in that field, I had a private practice it was very successful, but I realized, Tara, at some point that I had outgrown my interest and my willingness to hold space for people to feel better about where they were.

I was really growing impatient with them to move on from where they were. I think to really be a good therapist, you have to be able to be very present for people in whatever level of suffering they’re in and gently guide them out at the pace they’re able and willing to go. My philosophy at some point was “We have literally been talking about the same loss for five years, don’t you want to get on with the rest of your life?”

Now, obviously, that was my inside voice, I wasn’t sharing that but I happen to be noticed. My philosophy is that we’re all going to be dead in a minute, we don’t know if it’s literally a minute or if it’s going to be 30, 40 years from now, but life should be an adventure, it should be a journey, and we should always be developing ourselves, not necessarily checking off tasks, or I’m not talking about toxic productivity, I’m talking about developing ourself.

I felt at some point that I really wasn’t helping people move forward in their lives, I was helping them feel better about where they were and I just didn’t want to do that anymore. When I told the clients that I had at that time that I was closing the practice, I would refer them out to therapists if they wanted to continue with therapy, but the ones I thought could actually have been done with it and maybe work with a coach, they were not open to the idea.

While I do think there are a lot of coaches out there who are practicing therapy without a license, and I think a lot of potential harm is being done, haven’t been any high-profile cases that I’m aware of, but it’s just a matter of time, I also think the opposite is true that people can get just a little bit too comfortable in therapy mode, and as a result of that, fail to move forward in their life in a meaningful way. I’m not speaking to everybody in therapy, by no means, but you can get stranded there.

Tara Newman: To be honest, you can get stranded in coaching too. I think humans are remarkably resistant to progress even though it’s the thing that they want and that’s what holds people back in their businesses because women will come to me all the time and they’ll say, “How long is this going to take?” and I’m like, “Well, how long is it going to take you? How quickly can you move through discomfort, through healing?” and people are like, “Well, I need to heal and then do the things in my business,” and I’m like, “No, the healing comes through doing the things in the business and to challenging yourself,” so make that comparison for me to entrepreneurship, or like what you were just saying to entrepreneurship.

Diann Wingert: Yeah, what I learned, and tell me if I’m not answering the specific question because sometimes I think I am and I’m not and we can come back at it from a different angle, what I think is a lot of entrepreneurs, especially female entrepreneurs in my experience and observation, spend far too much time getting ready, they often think that I need one more certification. I need one more mastermind. I don’t feel ready to take this particular action, whether it’s starting the business, growing the business, scaling the business, hiring a team, whatever it is, if I don’t subjectively feel ready, it’s because I’m lacking something. I need to work with this particular coach, I need to join this particular group, or sometimes they think they need more therapy.

Oftentimes, they think they need more coaching, many times they think they need another certification. I recorded an episode for my podcast called There is No Magic Pill and it is because I think the industry, the online business industry, and the coaching industry, which oftentimes are the same, offer people the illusion of magic pills like, “Oh, six weeks to six figures or dream clients while you sleep,” and all this nonsense.

What actually moves your game piece forward is not thinking, it’s not planning, and it’s definitely not preparing, it is taking imperfect action. It is the only thing that moves the needle, it is the only thing that reveals to you what your actual sticking point is. The majority of us will do anything but that. You have to take action.

Unfortunately, when I first started doing this work, I don’t think I really leaned all the way into what a powerful change agent I’m capable of by allowing the client to take their sweet ass time. What I realized is that you have to require people to move forward if you actually want to have a transformation in working with you. If they’re not willing to take action, I don’t let them hire me anymore because they may feel inspired, they may feel informed, they may feel transformed, but if I can’t see tangible progress in the right direction with deliverables, I have failed them. I think you probably feel the same. You have to take action to learn what you need to do differently.

Tara Newman: I do feel the same and I have released clients with love and care saying, “I don’t think we can take this any further. It doesn’t make any sense for you to keep paying me at this point. I might not be the right person for you. This might not be the right avenue. I’m not really sure what that is but continuing on doing what we’re doing isn’t going to get you a different result.” I am here for implementation, so the Bold Profit Academy is an implementation container, implementation is what I actually do well. Doing the thing, let’s just take action, collect data, reassess, it’s a big science experiment, let’s put this business through the scientific method, but unless we’re willing to take action, we’re dead in the water. So I’m with you.

I see a lot of, especially women just waiting, and I don’t know if it’s waiting for permission, we need to be ready, waiting, waiting, waiting and I’m like, “Please, can we stop with the waiting? Can we please stop with the waiting? Could we please stop with the indecision. We need to make progress, ladies, it’s now, it’s go time.”

Diann Wingert: Yes, and you know what, I think you said a moment ago, Tara, that we don’t want to make progress, my take on it is we want to make progress without experiencing change. I do think that people with ADHD tend to be more friendly to change than others, it goes with the risk-taking however, some of us may be so change-friendly that we’re constantly changing our mind, changing our business model, changing our marketing strategy, that’s one of the other things that have to be reeled in because I’m all for experimentation, but if we don’t do something consistently enough, long enough, we don’t really have any data as to whether it worked or not so we can’t constantly change.

I think within the ADHD entrepreneur community, there tend to be either people that are very rigid who don’t want to change or they’re constantly, people call it shiny-object syndrome, they’re constantly trying something new because they’re looking for that magic pill. What I think we have to be able to do is, and I’ve actually empowered my team to do this with me because I’m constantly getting a new idea, and whatever new idea I’m getting is the best idea I’ve ever had because it’s hot off the press, I’m totally infatuated, it’s the best idea I’ve ever had, I have to stop everything I’m doing and chase this idea immediately.

I realized that I did that for many years and somebody said to me, “You’ll get a lot further down the field if you kick one soccer ball six times than if you kick six different soccer balls one time each.” I was like, “I don’t play soccer. Why are you even talking to me like this?” I understand it now and it’s being able to choose, of the millions of good ideas you have, the one you’re going to commit to doing, forsaking all others, like say your vows to this idea for a year and see how far you can move it down the game board. Because if you keep changing, which many of us tend to want to do, you’re just going to go around in circles and watch people who don’t know a third of what you know pass you by every day, which is infuriating.

Tara Newman: “But Diann, that’s boring, I don’t feel creative doing that. That doesn’t feel good in my body.” I’m just giving you what I hear. I want you to come back with the response.

Diann Wingert: Honey, especially with that whiny little tone, I’m having flashbacks here, okay, the truth is we do have a low threshold, we have a low threshold for boredom and we have a low tolerance of boredom, but what actually makes you successful in business is probably not going to be super exciting every single day. You have to find ways to be creative and ways to get your needs met, but it’s not your business’s job to excite you. We give our businesses jobs that they’re not meant to carry. I do think you absolutely have to find ways to make things fun so that you can sustain them.

One of the ways I do it is there are some things that are not that intrinsically interesting to me in my business and sometimes what you need to do is hire someone to do them for you because you know they’re important, you know they move your game piece, and you literally freaking despise them, you would rather stab yourself in the eye with a fork, so don’t try to do it. Get someone else to do it.

But if you have to do it and you’re resisting it, can you find a more creative way to do it? If you can’t do that, then I play beat the clock, I have a big ass timer. Because most of us have always been late, running late, barely getting anywhere at the last minute, and that is part of the ADHD personality type. So leverage that in your business by assigning a period of time to get that boring task done, play beat the clock, see how quickly you can get it done, and then give yourself a freaking reward. You can do that.

Tara Newman: Yeah. I’m big on asking the question “What would make this fun? What would feel exciting about doing this? How can we do this in a way that is energizing for you?” Because I think a lot of times we get stuck in black or white thinking it’s either this way or that way, this way, that way. It’s very binary and the reality is it’s not. We can get to the result in a lot of different ways but how can we get to the result in the quickest, most energizing, and fun way even if it’s something that maybe doesn’t feel fun?

Let’s face it, for me, working with people on sales, nobody thinks sales is fun initially but you are the commissioned salesperson in your business so if you want to eat, put food on your table, create profit, create the wealth that you want to create in your life, we need to figure out a way to do that in a way that feels fun and energizing in an alignment with your values and your strengths.

There are lots of ways that we can be creative in doing that but I really appreciate you sharing the message that you did. I love teeing up my guests to deliver hard messages that I’ve delivered, but sometimes I think don’t get through because it’s me, so they just need to hear it in a different voice. Thank you very much for that, Diann.

The other thing that I want to just challenge as well, and maybe you have a solution to this or we can talk about it, what about the using ADHD or ADHD traits, I don’t want to use the word excuse but I’m going to use the word excuse because I don’t have another word to use right now and so feel free to correct me, “But I do this because I’m ADHD, I can’t do this because I’m ADHD, I can’t batch my content because I’m ADHD, I can’t be consistent with anything because #ADHD,” and I gotta tell you something, I am the most consistent human known to man because I’m convinced, because of my ADHD, because I’ve had to teach myself how to do this, and that has made all the difference.

Because I keep hearing from people, “Sales are just dripping, dribbling in,” or “I’m tired of feeling like I’m always starting over,” well, those two things could easily be solved when you know what the right tasks are to do and then you do them every day. If we want to be “I want to make money every day,” well then you have to do the making money tasks every day.

Diann Wingert: Yeah, it’s true. Everything in our business isn’t sexy and everything in our business isn’t fun. I think, like you said before, I used to teach time management, and then as time went on and I worked with more and more people, I started teaching energy management, now I teach expectation management, and it incorporates all of those things. I think about what we expect of ourselves and what we expect of others and there are usually a lot of emotions around that.

Now I think some people they call out, “Oh, it’s the Millennials,” I’m like, “No, don’t do that. There are people of all generations who think things should be more easy and more fun than they actually are. It’s not just the Millennials, and by the way, the boomers are responsible for them so how’s that working for you?” Because usually, the people that are complaining are boomers. The reality is when I used to train people to be clinical social workers, one of the first questions I asked them in the interview to screen whether I was going to become their supervisor or whether I was going to assign them to someone else’s, “Tell me why you’re in this business? Why did you decide to become a therapist? I think everybody has a story for why they do what they do and I am interested in people’s stories, so how did you come into this? In this case, why did you decide to start a business?”

I’m listening for certain things and then I ask them, “And how long do you want to stay in business?” Now, people usually are a little off put by these questions because they’re just not used to being asked. First of all, if all the social media posts that you have been exposed to for the last five years tell you that you want to be a boss babe, you want to own a business, and you want to make money in your sleep, then you don’t even know why you think you want a business and you might not actually want one.

When we ask people “Why do you want a business? Tell me everything, and then how long do you want to stay in business?” some people know from the beginning “I just want to grow it to a certain point and then I want to get someone else to run it for me while I go do whatever, or I want to grow it to a certain point and then I want to sell it.” Most people haven’t really thought it through just like they haven’t thought through a lot of the money stuff, they haven’t thought through a lot of the profit stuff.

Sadly, this has been true of me too. Most people give up a job to start a business that ends up just being a job without benefits. That’s a hard uncomfortable truth that most of us aren’t facing. When we’re not facing the fundamental truth that we haven’t set up our business to generate wealth and to be profitable, we expect things of that business that are grossly unrealistic, we expect it to be fulfilling, we expect it to be exciting, we expect to want to get up every day, “Just can’t wait to get my butt in the chair and start creating content or seeing clients,” or whatever.

I don’t know of anyone who has that every single day, so I think the hard work that some of us actually need to do that we’re not doing is to develop the self-awareness and the insight through experimentation and asking ourselves good questions that we haven’t asked, “When am I at my most creative? What environment helps me focus more easily? How many hours can I work at a stretch without feeling bored, depleted, or whatever?” I believe that working for ourselves represents the single greatest opportunity to craft a business and lifestyle around our strengths and struggles, but most of us don’t do that work, we just copy what some internet guru is doing and then wonder why we’re not loving it.

Do the work and figure out when are you creative, when are you tired, when are you frustrated, when can you focus better. You can literally crop the business around that, and I’ll tell you this, I’ve been living with chronic pain for half my life. I had a very bad car accident. It left me with chronic pain that I’ve been living with for a very long time so I wake up early, I have energy for five hours, and then I need a three-hour break before I can work anymore.

I eat, I read, and I take a nap. It’s like a split shift, I couldn’t have done that if I was working for someone else so I created that for myself. I know how many consecutive hours I can work without losing focus or getting fatigued, or I know how many people I can interview from my podcast in a row before I’m not showing up as my best.

I’m curious like you and I was willing to spend the time to figure out what kind of business would serve me best and allow me to sustain it for as long as I want to. I think instead of expecting our business to entertain us or make us feel good about ourselves without effort, we need to be willing to expend a little bit of effort to create a business that can do all that and more, and it’s not automagic or overnight. Did that answer your question?

Tara Newman: Full stop. That’s a wrap. Yeah, no, listen, that was brilliant, true, and poignant. I hope that everybody just hits rewind and listens to that quite a few times because I have people who, when we talk about business values and they say, “Oh, my business value is adventure,” I’m like, “No, are you sure? Because I think your personal value is adventure, and in that case, you want your business to be as simple as possible so that you can go and have those adventures.” I don’t want my business to be adventurous. I like adventure, but I want my business to be as simple as possible so that I can go have those adventures somewhere else in my life.

I think what you touched on there about all the reasons why you wanted to have a business and how you spend your day really elucidates a point that I’ve been trying to make, women think they want an “online business” but what they actually want is what Diann just shared, they want something that is fully remote that you don’t need to be going into an office and on somebody else’s schedule, you want a non-linear schedule that is exactly what Diann has. She has her energy in the morning, she takes a break in the middle of the day, she comes back to her work. I do the same, and we want to be able to have a way of working that allows us to do the deep, focused work without distraction because that is where our most important work comes from, the thing that we are the most proud of is in that creativity of deep work, that deep work allows for.

What people and women actually want is a fully remote business that allows them to work asynchronously for deep work purposes and non-linearly for energetic purposes. Online business and online business models are the exact opposite of what they actually want. So thank you. Thank you very much for sharing that. Where can people find you? Because I want them to go and find you. You have a podcast, you have other things.

Diann Wingert: The podcast, I like to say if you like the sound of my voice and what I have to say with it, you don’t mind a little salty language and very direct opinions, then you’re going to want to head on over in your podcast player to The Driven Woman Entrepreneur. There’s a very cute picture of me and my pre-COVID body with a big smile flexing, and you can find my website at There’s a fun quiz on that website called What’s Holding Me Back? I’m sure Tara will also pop it into the show notes to make it easy peasy for you to take it.

Tara Newman: Absolutely, Diann, and is there something you want to leave the audience with, something that you’ve left unsaid so far?

Diann Wingert: Oh, I think we covered a lot of territory. I would say that I think the most significant thing we need to do as a woman in business is to let people know all of who we really are and be willing to fully accept the consequences of that decision. Your most powerful self, your most genuine self, your awesome sauce, your magic, your unfair advantage, what you are literally here to share will never be fully experienced if you are people-pleasing and following other gurus. You be the freaking guru, you lead the people you’re here to lead. Nobody can teach you how to do that. You take the steps. You find your way.

Tara Newman: Oh, we’re leaving it there. Thanks, Diann. Thank you for coming on.

Diann Wingert: My pleasure.